I smacked down the map of Harpswell on my kitchen table and circled eight locations around the town, connecting them with lines like a TV detective stumped by a high-profile case.
I was attempting to complete the 13th annual Harpswell Hiking Challenge in one day.
I had arrived in Harpswell a week prior to spend the summer as a news intern at the Anchor, so the challenge allowed me to explore not only Harpswell’s trails but also the town itself.
Just after 10:30 a.m., I reached Hiking Challenge headquarters at the Town Office. I etched my name onto the sign-up sheet to kick-start a day of unbelievably scenic views and equally sore knees.
The annual event invites participants to complete eight hikes around Harpswell in the span of a weekend, or four in a modified version. Gina Caldwell, the town’s recreation director and community services coordinator, said 70 people signed up this year.
“It gets people outside,” Caldwell said. “It’s a great introduction to our trails.”
The volunteers told me a couple of go-getters began at 4:30 a.m. and were done by the time headquarters opened at 9.
Each trail had a unique hole punch attached to a stake. To complete the challenge and earn a fluorescent pink T-shirt, each hiker had to collect all eight punches on a sheet of paper.
The first trail I embarked on was Cliff Trail, because of its convenient location behind the Town Office. The longest hike of the day was also my most anticipated, with praise from both locals and the internet.
The trail was designated as a “storybook trail” — a separate initiative that nonetheless added to the event. Pages of the children’s book “Mother Bruce,” by Ryan T. Higgins, were set up throughout the hike. “Mother Bruce” is the story of a grumpy bear who lived by himself before motherhood was thrust upon him when the eggs he bought for breakfast hatched. Everyone I encountered along the trail, regardless of age, was engrossed in the charming story.
I then ran into Katie Wright, a participant on her fourth trail. Wright, who has completed the challenge in prior years, said it was an excuse to go hiking.
“It’s nice to move towards a goal for a day,” she added.
The airplane-shaped hole punch was a fitting reward for the heights reached, but the true prize was the view of Long Reach from the cliff’s edge.
A seemingly endless wall of pines served as a frame for Harpswell’s natural magnum opus. However, I couldn’t linger too long, as seven more trails were waiting.
The trail at Curtis Farm Preserve began in an open field on the grounds of an old homestead before curving into a tunnel of trees and ending at Curtis Cove.
On the way back, I ran into Sandy Vance, who had heard of the challenge through Facebook. Vance had wanted to get back into hiking, but felt hesitant about doing so alone.
“On a personal level, I won, because I did some solo hiking,” Vance said.
Later in the hike, I found the lack of trail markers on trees to be a concern. As I wandered aimlessly, two words on my notepad explained my situation: “VERY LOST.”
“Are there moose and black bears in Harpswell?” I wondered. That thought was followed by, “Do coyotes eat humans?”
After a couple of minutes, I saw two hikers in the distance and, relieved, returned to the path.
My next stop was Mitchell Field. My brain went into autopilot and my steps seemed to turn the wheel in my brain onto different thoughts, such as: “I hope I don’t get lost again” and “I could use a coffee.”
So, after completing the 1.6-mile loop, I collected an iced latte to reenergize.
I then parked at the Harpswell Historical Society Museum for the Hackett and Minot Trails across the street.
The trail felt surreal, as if designed by the brothers Grimm. The hushed, narrow path weaves deep into the woods, so deep that I half-expected to come across a cleverly disguised wolf or a short man spinning straw into gold.
A 24-minute drive, soundtracked by my ’80s rock playlist, took me across town to Little Ponds Preserve. Whether it was the lengthy drive or the only noise being skittish chipmunks, this trail felt the most remote.
Next, on Orr’s Island, the east side of the Devil’s Back Trail Area began high on the road, working its way down with a breathtaking view of emerald waters veiled by a row of towering conifers.
My penultimate hike took me across the street to the west side of Devil’s Back. This trail mirrored its eastern counterpart in its design and stunning beauty. I was so distracted by the view that the Hiking Challenge had escaped my mind entirely when I ran into the hole punch.
As I neared the water, a quick-moving man in a fur cap and what appeared to be a Scout’s uniform agreed: “Gorgeous, isn’t it?”
I learned that last year’s challenge was marred by two days of rain. This year was a vast improvement, with pastel skies and sun overcompensating for 2023’s transgression.
Finally, I ended up across from Harpswell Community School. Here, I ran into volunteers Ken and Sharon Oehmig, who told me about Harpswell’s newest trail through my final stop, the Anna M. Tondreau Preserve.
While all the trails were new to an outsider like myself, I was excited at the novelty of the Tondreau trail. The opportunity to be a sort of Neil Armstrong on an untouched land was exciting. However, the footprints in the mud at the trailhead made me more of a Buzz Aldrin.
The trail boasts a small stream, wooden bridges and mossy rocks. I then reached my last station and a tree-shaped hole punch marking the completion of an arduous and adventurous day.
I climbed into my car with the playlist shuffling through Aerosmith’s hits and a new T-shirt at my side. My legs ached from more than 10 miles of hiking, my stomach growled like I imagined Bruce the bear would, and the last drop in my water bottle was gone. However, a day of nature, community and exercise was one I would enthusiastically repeat.
Mary Connolly, a volunteer with the Harpswell Heritage Land Trust, summarized it to perfection.
“It’s about exploring,” Connolly said. “It highlights the beauty of Harpswell.”
